In pursuit of what makes companies successful
What I've learned so far and five things I'd do if I started my own company
Lately, I’ve started to ponder the longer term trajectory of my career. Not in a very active way – just an occasional passive, background murmur that sometimes flutters into my consciousness when I start to think about how I’m doing at work.
When I was in consulting, there was a clearly laid out path and timeline for each tenure, and there were many levels through which to advance. There was always a target for the next promotion and the criteria to make that promotion were generally fairly objective. Barring crazy economic uncertainty (hello, world of today), you could generally rely on doing your part and progressing as expected.
People would always tell junior consultants that consulting accelerated your career: “Do three years here and exit into a role that’s intended for someone with more than five years of experience.” And then sometimes, when someone wanted to make the argument for why to stay in consulting, they’d say, “Well, in industry, there’s nowhere to be promoted unless the person above you retires or leaves. You’ll be stuck in the same role forever.”
Now obviously, that’s not the full story. In industry, there are promotions within levels that can happen every few years and then there are promotions into subsequent levels as well. And beyond that, as I think about my longer term career trajectory, there are so many more factors than just promotions and titles.
For me, it’s looking for answers to one of the biggest questions I’ve always had. Starting in college, I began to wonder how the companies that look successful are actually run on the inside. Is it really the result of good leadership, or is there more to it than just that? And what does good leadership look like anyway?
Now, before I proceed any further, I will share a big disclaimer/caveat:
No matter how successful the company, the inner workings will always be messy. I have data points on this from friends who’ve worked at the likes of Microsoft, Google, Meta, etc. There are always more things to be fixed, processes to be improved, additional feedback to be given. It’s never perfect.
I know this truth now. I did not know this when I was 21 years old and starting out my career. I thought I’d find the cheatsheet and all the answers in consulting. However, it turns out that you see either the companies that aren’t being run super well or instead, the ones where things have been run the same way for decades and they’re good enough.
So, suffice it to say I was somewhat disappointed on this front when I left consulting. I continued to look for the answers to this big question.
At the startup I joined, I became part of the leadership team and I was thrown into the deep end – I was suddenly in the room where we were making all these decisions that impacted the success of the company. Quickly, I learned firsthand some things about what works and what doesn’t work. That said, it didn’t really satisfy my curiosity as we were just learning through trial and error and often didn’t have access to tactical answers from anyone who had more wisdom on the matter.
Fast forward to the end of my gap year when I was looking for my next role – I decided that a big priority needed to be going somewhere where I’d have models of good leadership and be able to see how successful companies operate on the inside.
I recently found a list where I had jotted down some ideas and thought I’d share them as my hot takes on company building. Most of these were formulated over the past four-ish years, but I’ve also added to and edited them over time as I’ve seen more datapoints.
Plan for the year in thirds, not quarters. In my experience, planning takes up so much time, no matter how efficiently the team tries to do it. In addition to just the admin overhead associated with it (meetings, documents, summaries, Slack messages, etc.), there’s also the context switching and opportunity cost on senior leadership. What if, instead of quarterly planning, we got an extra month of mileage once the team is in the zone and heads down on building for roughly the same amount of planning? Plus, it’s easier to offset planning cycles from summer slowdown months and end of year holidays.
Don’t bloat the tech stack – minimize the tools the team has. This might be my personal favourite because it’s such a curveball for someone who spent 2.5 years entrenched in the business of making it easier to buy software. But my honest reflection is that every time a new tool is selected, purchased, and set up, it is extremely expensive to the team. New processes have to be created and adopted, change has to be managed, and, worst of all, if this goes poorly, then time and money have both been wasted. Many tasks can be consolidated into existing tools – never underestimate the power of a spreadsheet. Yes, certain tools will be worth the squeeze, but not all of them – be discerning and just as you wouldn’t preemptively hire headcount before there’s enough work to go around, stretch every tool to its limit before you add to the stack.
Be open to feedback from your team, but train them to hear “No” as well. Upward feedback is a wonderful gift – whether it’s feedback on the leadership team, company-wide processes or other decisions that shape the day-to-day. Be open to it and make it easy and comfortable for the team to give, but also don’t falsely promise that it will all be addressed. The team needs to be open to answers like “We can’t do that because we don’t believe in it” or “We can’t do that right now given our size and constraints.” One of the biggest mistakes is opening the floodgates for feedback without setting boundaries.
Leaders should have a mentality of servanthood when it comes to ops but never when it comes to strategy and decision making. Meaning, when push comes to shove, the best leaders are the ones who roll up their sleeves and help make things happen. There is no task that is “too small” or “below” someone based on their tenure. However, when it comes to setting the direction of the company – i.e. setting the strategy and making crucial decisions – leadership needs to have strong convictions that cannot waver even under pushback from the rest of the team. That’s how it all starts to fall apart.
Everyone should try someone else’s job at some point. Not only does redundancy of knowledge matter at a fundamental level within each team (think, bus factor), it also matters across teams. It starts with cross-team empathy that deepens to understanding and eventually the ability to substitute for one another. This isn’t an expectation for every single person in every single direction, but rather each individual should have a grasp of a few other people’s roles within the company. This makes them better big picture thinkers and also ensures that the systems that each team is building are not siloed and instead, will play nicely with each other. And, in dire circumstances, this provides a better chance at redundancy that allows for cross coverage.
Did these resonate, or did they stoke a little flame of disagreement in you? Tell me in the comments!